With AI-generated content becoming ubiquitous across the web, social media, and other digital platforms, it is vital to examine how such content are inspired and generated. The creation of AI-generated images often involves refining the input prompt iteratively to achieve desired visual outcomes. This study focuses on the relatively underexplored concept of image regeneration using AI, in which a human operator attempts to closely recreate a specific target image by iteratively refining their prompt. Image regeneration is distinct from normal image generation, which lacks any predefined visual reference. A separate challenge lies in determining whether existing image similarity metrics (ISMs) can provide reliable, objective feedback in iterative workflows, given that we do not fully understand if subjective human judgments of similarity align with these metrics. Consequently, we must first validate their alignment with human perception before assessing their potential as a feedback mechanism in the iterative prompt refinement process. To address these research gaps, we present a structured user study evaluating how iterative prompt refinement affects the similarity of regenerated images relative to their targets, while also examining whether ISMs capture the same improvements perceived by human observers. Our findings suggest that incremental prompt adjustments substantially improve alignment, verified through both subjective evaluations and quantitative measures, underscoring the broader potential of iterative workflows to enhance generative AI content creation across various application domains.